Growing up in the old West End in the 1950s, Bobby Dellelo mastered stealing cars before he knew how to drive one.

Trouble found him early. He graduated from routine burglaries as a teenager to more sophisticated robberies. During one appalling episode, he and a friend attempted to rob a liquor store in Dorchester. They marched the store’s customers, at gunpoint, into a freezer. As other customers arrived, they put them in the freezer, too. Then they took the money and ran.

Dellelo eventually served more than two years for that heist, along with another robbery.

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But the crime that has come to define him involved the murder of a Boston ­police office in 1963. Dellelo and an accom­plice attempted to rob a
jewelry store on Washington Street. After the store’s alarm sounded, they abandoned their plan and ran their separate ways. But Dellelo’s accomplice shot and killed Detective George Holmes before turning the gun on himself.

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Of the nearly 40 years he served, five years and one month were in solitary confinement, in a cell he described to me as “12 feet long, 8 feet wide, and 10 feet high.”

He landed in solitary after successfully escaping from prison and being recaptured. At first he was unconcerned.

“I thought it would be a piece of cake,” he said.

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It was not a piece of cake. He was alone for a minimum of 23 hours a day. He had a radio and a small television in his cell, and after a while, both began to drive him crazy — literally crazy. “Static wasn’t just static,” he says by way of explanation. “It was speaking a language. It was speaking to me.” He put his TV in a corner and tried to forget about it.

When Dellelo’s lawyer came to visit, he discovered just how far removed he had become from human contact. Though he spoke to guards from his cell, he wasn’t accustomed to talking to someone he could actually see.

“Every time she moved her arm I lost my train of thought,” he says. “What happened to me was body language and verbal skills go hand-in-hand. When you separate them, chaos ensues.”

Dellelo has become sort of a philosopher of solitary confinement.

He is not the only person thinking about the wisdom of this time-honored method of incarceration. This week, state Senator Jamie ­Eldridge, Democrat of ­Acton, is filing legislation to curb the use of solitary confinement. Under the legislation, prisoners in solitary would receive a hearing after 15 days to determine whether they pose a danger to themselves or other prisoners. Following that, prisoners would be entitled to a hearing every 90 days to determine whether they should remain in isolation.

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Eldridge, a former legal aid lawyer, says his concern stems partly from having two state prisons in his district. “I happen to think it’s cruel and unusual punishment for someone to be in a cell 23 hours a day,” he said last week. “Every year I take a tour of the prisons in my district and being in one of those cells for even five minutes really hits me.”

Dellelo’s murder conviction was eventually reduced to manslaughter, and he was released in 2003. He immediately ­became a volunteer for the American Friends Service Committee, counseling prisoners and released convicts. He ­believes there is a need for solitary confinement, but on a far more limited basis.

He maintains, from experience, that isolation makes rejoining society more difficult. When he got out, his familiar landmarks and routines were all gone. Not only that, he had to cope with other people.

“The first time I rode a bus and the doors opened, all these people came rushing in,” he recalled. “I had an instant panic attack.”